Cholesteryl ester

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Cholesterol oleate, a member of the cholesteryl ester family Cholesterol oleate.svg
Cholesterol oleate, a member of the cholesteryl ester family

Cholesteryl ester, a dietary lipid, is an ester of cholesterol. The ester bond is formed between the carboxylate group of a fatty acid and the hydroxyl group of cholesterol. Cholesteryl esters have a lower solubility in water due to their increased hydrophobicity. Esters are formed by replacing at least one –OH (hydroxyl) group with an –O–alkyl (alkoxy) group. They are hydrolyzed by pancreatic enzymes, cholesterol esterase, to produce cholesterol and free fatty acids. [1] They are associated with atherosclerosis. [2]

Cholesteryl ester is found in human brains as lipid droplets which store and transport cholesterol. [3] Increased levels of cholesteryl ester have been found in certain parts of the brain of people with Huntington disease. Higher concentrations of cholesteryl ester have been found in the caudate and putamen, but not the cerebellum, of people with Huntington disease compared with levels in controls. [4] Increase in cholesteryl ester has also been found in other neurological disorders like multiple sclerosis and Alzheimer’s disease. [3]

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Cholesterol is the principal sterol of all higher animals, distributed in body tissues, especially the brain and spinal cord, and in animal fats and oils.

<span class="mw-page-title-main">Fat</span> Esters of fatty acid or triglycerides

In nutrition, biology, and chemistry, fat usually means any ester of fatty acids, or a mixture of such compounds, most commonly those that occur in living beings or in food.

High-density lipoprotein (HDL) is one of the five major groups of lipoproteins. Lipoproteins are complex particles composed of multiple proteins which transport all fat molecules (lipids) around the body within the water outside cells. They are typically composed of 80–100 proteins per particle. HDL particles enlarge while circulating in the blood, aggregating more fat molecules and transporting up to hundreds of fat molecules per particle.

<span class="mw-page-title-main">Low-density lipoprotein</span> One of the five major groups of lipoprotein

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<span class="mw-page-title-main">Lipoprotein</span> Biochemical assembly whose purpose is to transport hydrophobic lipid molecules

A lipoprotein is a biochemical assembly whose primary function is to transport hydrophobic lipid molecules in water, as in blood plasma or other extracellular fluids. They consist of a triglyceride and cholesterol center, surrounded by a phospholipid outer shell, with the hydrophilic portions oriented outward toward the surrounding water and lipophilic portions oriented inward toward the lipid center. A special kind of protein, called apolipoprotein, is embedded in the outer shell, both stabilising the complex and giving it a functional identity that determines its role.

<span class="mw-page-title-main">Carnitine</span> Amino acid active in mitochondria

Carnitine is a quaternary ammonium compound involved in metabolism in most mammals, plants, and some bacteria. In support of energy metabolism, carnitine transports long-chain fatty acids from the cytosol into mitochondria to be oxidized for free energy production, and also participates in removing products of metabolism from cells. Given its key metabolic roles, carnitine is concentrated in tissues like skeletal and cardiac muscle that metabolize fatty acids as an energy source. Generally individuals, including strict vegetarians, synthesize enough L-carnitine in vivo.

<span class="mw-page-title-main">Stanol ester</span> Class of chemical compounds

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<span class="mw-page-title-main">Lecithin–cholesterol acyltransferase</span> Mammalian protein found in Homo sapiens

Lecithin–cholesterol acyltransferase is an enzyme, in many animals including humans, that converts free cholesterol into cholesteryl ester, which is then sequestered into the core of a lipoprotein particle, eventually making the newly synthesized HDL spherical and forcing the reaction to become unidirectional since the particles are removed from the surface. The enzyme is bound to high-density lipoproteins (HDLs) (alpha-LCAT) and LDLs (beta-LCAT) in the blood plasma. LCAT deficiency can cause impaired vision due to cholesterol corneal opacities, anemia, and kidney damage. It belongs to the family of phospholipid:diacylglycerol acyltransferases.

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Hormone-sensitive lipase (EC 3.1.1.79, HSL), also previously known as cholesteryl ester hydrolase (CEH), sometimes referred to as triacylglycerol lipase, is an enzyme that, in humans, is encoded by the LIPE gene, and catalyzes the following reaction:

Lysosomal lipase is a form of lipase which functions intracellularly, in the lysosomes.

Blood lipids are lipids in the blood, either free or bound to other molecules. They are mostly transported in a phospholipid capsule, and the type of protein embedded in this outer shell determines the fate of the particle and its influence on metabolism. Examples of these lipids include cholesterol and triglycerides. The concentration of blood lipids depends on intake and excretion from the intestine, and uptake and secretion from cells. Hyperlipidemia is the presence of elevated or abnormal levels of lipids and/or lipoproteins in the blood, and is a major risk factor for cardiovascular disease.

Sterol O-acyltransferase is an intracellular protein located in the endoplasmic reticulum that forms cholesteryl esters from cholesterol.

<span class="mw-page-title-main">Ethyl eicosapentaenoic acid</span> Medication

Ethyl eicosapentaenoic acid, sold under the brand name Vascepa among others, is a medication used to treat dyslipidemia and hypertriglyceridemia. It is used in combination with changes in diet in adults with hypertriglyceridemia ≥ 150 mg/dL. Further, it is often required to be used with a statin.

<span class="mw-page-title-main">Lysosomal acid lipase deficiency</span> Medical condition

Lysosomal acid lipase deficiency is an autosomal recessive inborn error of metabolism that results in the body not producing enough active lysosomal acid lipase (LAL) enzyme. This enzyme plays an important role in breaking down fatty material in the body. Infants, children and adults that have LAL deficiency experience a range of serious health problems. The lack of the LAL enzyme can lead to a build-up of fatty material in a number of body organs including the liver, spleen, gut, in the wall of blood vessels and other important organs.

<span class="mw-page-title-main">Evacetrapib</span> Chemical compound

Evacetrapib was a drug under development by Eli Lilly & Company that inhibits cholesterylester transfer protein. CETP collects triglycerides from very low-density lipoproteins (VLDL) or low-density lipoproteins (LDL) and exchanges them for cholesteryl esters from high-density lipoproteins (HDL), and vice versa, but primarily increasing high-density lipoprotein and lowering low-density lipoprotein. It is thought that modifying lipoprotein levels modifies the risk of cardiovascular disease. The first CETP inhibitor, torcetrapib, was unsuccessful because it increased levels of the hormone aldosterone and increased blood pressure, which led to excess cardiac events when it was studied. Evacetrapib does not have the same effect. When studied in a small clinical trial in people with elevated LDL and low HDL, significant improvements were noted in their lipid profile.

References

  1. Ferrier, Richard A. Harvey, Denise R. (2011). Lippincott's illustrated reviews, biochemistry (5th ed.). Philadelphia: Wolters Kluwer Health. p. 175. ISBN   9781608314126.
  2. Cholesterol+Esters at the U.S. National Library of Medicine Medical Subject Headings (MeSH)
  3. 1 2 Phillips, Gabrielle R.; Hancock, Sarah E.; Brown, Simon H. J.; Jenner, Andrew M.; Kreilaus, Fabian; Newell, Kelly A.; Mitchell, Todd W. (2020-11-20). "Cholesteryl ester levels are elevated in the caudate and putamen of Huntington's disease patients". Scientific Reports. 10 (1): 20314. Bibcode:2020NatSR..1020314P. doi: 10.1038/s41598-020-76973-8 . ISSN   2045-2322. PMC   7680097 . PMID   33219259.
  4. "Illawarra Health and Medical Research Institute Researchers Report on Findings in Huntington Disease (Cholesteryl ester levels are elevated in the caudate and putamen of Huntington's disease patients) (Cholesteryl ester levels are elevated in ...)." Obesity, Fitness & Wellness Week, 2020, p. 2684. Gale Academic OneFile, link.gale.com/apps/doc/A643924682/AONE?u=cuny_hunter&sid=AONE&xid=6782d457. Accessed 2 May 2021.